Hydrogen Bromide → 4,4'-(2,2,2-Trifluoro-1-phenylethane-1,1-diyl)diphenol

HRID 6196

반응식

HRID 6196 반응식
F[C:2](F)(F)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[F:13][C:14]([F:20])([F:19])S(O)(=O)=O.[C:21]1([O:27]C)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Br>C(O)(=O)C>[OH:27][C:21]1[CH:26]=[CH:25][C:2]([C:3]([C:24]2[CH:23]=[CH:22][C:21]([OH:27])=[CH:26][CH:25]=2)([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:14]([F:20])([F:19])[F:13])=[CH:23][CH:22]=1

참가 물질

6

반응물 4

HCID 260Hydrogen BromideHCID 7519AnisoleHCID 99052,2,2-TrifluoroacetophenoneHCID 62406Trifluoromethanesulfonic acid

생성물 1

HCID 190051754,4'-(2,2,2-Trifluoro-1-phenylethane-1,1-diyl)diphenol

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A mixture of 100 grams (0.57 mol) of trifluoroacetophenone, 100 grams (0.7 mol) trifluoromethane sulfonic acid, and 100 grams (10.9 mol) anisole is stirred at room temperature for 24 hours. The mixture is then transferred to a separatory funnel and the organic material is washed with water (3×11), saturated bicarbonate (3×500 ml) and water (2×500 ml). The organic phase is dried and the volatiles removed in vacuo. The resulting material is crystallized from aqueous methanol. 37.2 grams (0.1 mol) of this product is refluxed with glacial acetic acid saturated with anhydrous hydrobromic acid. The mixture is cooled and poured over crushed ice and the solid collected. The crude material is recrystallized from ethanol and petroleum ether to give 1,1-bis(4-hydroxyphenyl)-1-phenyl-2,2,2-trifluoroethane.

후처리

  1. customThe mixture is then transferred to a separatory funnel
  2. washthe organic material is washed with water (3×11), saturated bicarbonate (3×500 ml) and water (2×500 ml)
  3. customThe organic phase is dried
  4. customthe volatiles removed in vacuo
  5. customThe resulting material is crystallized from aqueous methanol
  6. temperatureThe mixture is cooled
  7. additionpoured
  8. customover crushed ice
  9. customthe solid collected
  10. customThe crude material is recrystallized from ethanol and petroleum ether

출처 및 근거

ORD 기록
ord-7ba62443ec7649e18842d3f4e41dec27
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05247050

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